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ActiveListed 26 days ago

$1,750,000

1 Overlook Way, Winchester, MA 01890

4
beds
2.5
baths
3,604
sqft
Lot sizeThe land that comes with the home, as reported to the MLS.
0.36 acres
Year builtThe year the building was originally built, as reported by the listing agent.
1941
On the marketDays since the home was listed. New listings tend to move fastest.
26 days ago
Property type
Single Family Residence
Price per sqftList price divided by interior living area — handy for comparing homes of different sizes.
$486
ParkingSpaces that come with the home, as reported to the MLS.
6 spaces
Annual taxesLast annual property tax bill reported to the MLS. A new owner's bill can differ.
$17,650

What’s Special

  • Fireplace
  • Patio
  • In Basement

Welcome to One Overlook Way in Winchester. This spacious 4+ bedroom center-entrance Colonial is tucked away on a short cul-de-sac off High Street, in a premier location close to Ambrose Elementary School and the Winchester Country Club. The foyer opens to a thoughtfully designed floor plan with wonderful flow for everyday living and entertaining. The generously sized eat-in kitchen features stone countertops and stainless steel appliances and connects to the beautiful dining room. The kitchen also opens naturally into the cozy family room - with gas fireplace, custom built-ins and access to the back and side yard, the family room will be well utilized! A larger front-to-back living room with fireplace and box windows is located off the foyer and is complemented by an adjoining oversized library or playroom. Upstairs, the spacious primary suite offers a private bath with double vanity, full shower and great closet space. Three additional bedrooms feature hardwood floors, generous closets and access to a shared full bath. The third-floor bonus space provides flexible room for guests, a home office or storage. The finished lower level adds even more usable space, with a fireplace and room for exercise, hobbies or relaxation. Enjoy the outdoors in this large, level yard with established plantings, brick patio and plenty of space to entertain. There is a two-car garage plus 300+sf of unfinished space above the garage. Please ask the agent for more information. This home truly has it all. This is one home you do not want to miss.

Listing courtesy of Lynne Russo, Better Homes and Gardens Real Estate - The Shanahan Group · MLS PIN #73581571

Facts & Features

Status
Active
Active status flag
Active
Bedrooms
4
Bathrooms
2 full, 1 half
Living area
3,604 sqft

Interior

8
  • Closet/Cabinets - Custom Built
  • Walk-In Closet(s)
  • Cedar Closet(s)
  • Storage
  • Library
  • Bonus Room
  • Play Room
  • Walk-up Attic

Exterior

5
  • Patio
  • Rain Gutters
  • Sprinkler System
  • Screens
  • Stone Wall

Parking

5
  • Attached
  • Garage Door Opener
  • Paved Drive
  • Off Street
  • Paved

Laundry

3
  • Gas Dryer Hookup
  • Washer Hookup
  • In Basement

Heating

5
  • Central
  • Baseboard
  • Natural Gas
  • Ductless
  • Fireplace

Cooling

1
  • Ductless

Appliances

8
  • Gas Water Heater
  • Range
  • Dishwasher
  • Trash Compactor
  • Microwave
  • Refrigerator
  • Washer
  • Dryer

MLS PIN #73581571 · Listed September 23, 2026

Location

1 Overlook Way, Winchester · All Winchester homes

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

$1,750,000

1 Overlook Way

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The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.